1197214-47-3

Usage

Uses

Used in Pharmaceutical Industry:
(1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol is used as a chiral resolving agent and chiral ligand for the production of pharmaceuticals. Its chiral properties allow for the synthesis of enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Agrochemical Industry:
In the agrochemical industry, (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol is utilized as a chiral ligand in asymmetric catalysis for the synthesis of enantiomerically pure agrochemicals. This ensures the production of active ingredients with desired properties and minimal environmental impact.
Used in Fine Chemicals Industry:
(1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol is employed as a chiral resolving agent and chiral ligand in the synthesis of fine chemicals. Its chiral nature and structural features contribute to the production of high-quality enantiomerically pure compounds for various applications.
Used in Synthesis of Optically Active Compounds:
(1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol is used as a key intermediate in the synthesis of optically active compounds. Its chiral properties enable the production of enantiomerically pure compounds with specific biological activities and applications.
Used in Analytical Chemistry for Chiral Separation:
In analytical chemistry, (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol is utilized for chiral separation techniques. Its unique structural features allow for the efficient separation of enantiomers, which is crucial for the analysis and characterization of chiral compounds in various fields.

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 78229-12-6 (Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 
• 791616-64-3 (R_a)-3,3’-dibromo-2,2’-bis(methoxymethoxy)-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene 
• 39648-74-3 (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol 

Relevant academic research and scientific papers

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

Highly enantioselective bromocyclization of tryptamines and its application in the synthesis of (-)-chimonanthine

A shorter path: A highly enantioselective bromocyclization of tryptamine has been developed using an anionic chiral phase-transfer catalyst. This method provides a direct approach for preparing chiral 3-bromopyrroloindoline from tryptamine, which enables a four-step enantioselective synthesis of (-)-chimonanthine. PG=protecting group. Copyright

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.